Regioselective Enzymatic Carboxylation of Bioactive (Poly)phenols

被引:24
作者
Plasch, Katharina [1 ]
Resch, Verena [1 ]
Hitce, Julien [2 ]
Poplonski, Jaroslaw [3 ]
Faber, Kurt [1 ]
Glueck, Silvia M. [1 ,4 ]
机构
[1] Graz Univ, Dept Chem Organ Bioorgan Chem, Heinrichstr 28, A-8010 Graz, Austria
[2] L Oreal Res & Innovat, 30 bis rue Maurice Berteaux, F-95500 Le Thillay, France
[3] Wroclaw Univ Environm & Life Sci, Dept Chem, ul C K Norwida 25, PL-50375 Wroclaw, Poland
[4] Graz Univ, Austrian Ctr Ind Biotechnol, Heinrichstr 28, A-8010 Graz, Austria
基金
奥地利科学基金会;
关键词
ortho-benzoic acid decarboxylases; bioactive (poly) phenols; biocatalysis; carboxylation; regioselectivity; KOLBE-SCHMITT REACTION; GAMMA-RESORCYLIC ACID; CATALYZING NONOXIDATIVE DECARBOXYLATION; P-AMINOSALICYLIC ACID; CARBON-DIOXIDE; 2,6-DIHYDROXYBENZOATE DECARBOXYLASE; HYDROXYSTYRENE DERIVATIVES; RHIZOBIUM-RADIOBACTER; ANAEROBIC METABOLISM; CHEMICAL FEEDSTOCK;
D O I
10.1002/adsc.201601046
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
In order to extend the applicability of the regioselective enzymatic carboxylation of phenols, the substrate scope of o-benzoic acid (de) carboxylases has been investigated towards complex molecules with an emphasis on flavouring agents and polyphenols possessing antioxidant properties. oHydroxycarboxylic acid products were obtained with perfect regioselectivity, in moderate to excellent yields. The applicability of this method was proven by the regioselective bio-carboxylation of resveratrol on a preparative scale with 95% yield.
引用
收藏
页码:959 / 965
页数:7
相关论文
共 61 条
  • [51] BIOCHEMICAL PROPERTIES OF ANTI-INFLAMMATORY DRUGS .V. UNCOUPLING OF OXIDATIVE PHOSPHORYLATION BY SOME GAMMA-RESORCYL AND OTHER DIHYDROXYBENZOL COMPOUNDS
    WHITEHOU.MW
    DEAN, PDG
    [J]. BIOCHEMICAL PHARMACOLOGY, 1965, 14 (04) : 557 - &
  • [52] Merging Sustainability with Organocatalysis in the Formation of Organic Carbonates by Using CO2 as a Feedstock
    Whiteoak, Christopher J.
    Nova, Ainara
    Maseras, Feliu
    Kleij, Arjan W.
    [J]. CHEMSUSCHEM, 2012, 5 (10) : 2032 - 2038
  • [53] Carbon dioxide fixation by reversible pyrrole-2-carboxylate decarboxylase and its application
    Wieser, M
    Yoshida, T
    Nagasawa, T
    [J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2001, 11 (4-6) : 179 - 184
  • [54] Regioselective Enzymatic β-Carboxylation of para-Hydroxystyrene Derivatives Catalyzed by Phenolic Acid Decarboxylases
    Wuensch, Christiane
    Pavkov-Keller, Tea
    Steinkellner, Georg
    Gross, Johannes
    Fuchs, Michael
    Hromic, Altijana
    Lyskowski, Andrzej
    Fauland, Kerstin
    Gruber, Karl
    Glueck, Silvia M.
    Faber, Kurt
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (08) : 1909 - 1918
  • [55] Regioselective ortho-carboxylation of phenols catalyzed by benzoic acid decarboxylases: a biocatalytic equivalent to the Kolbe-Schmitt reaction
    Wuensch, Christiane
    Gross, Johannes
    Steinkellner, Georg
    Lyskowski, Andrzej
    Gruber, Karl
    Glueck, Silvia M.
    Faber, Kurt
    [J]. RSC ADVANCES, 2014, 4 (19): : 9673 - 9679
  • [56] Regioselective Enzymatic Carboxylation of Phenols and Hydroxystyrene Derivatives
    Wuensch, Christiane
    Glueck, Silvia M.
    Gross, Johannes
    Koszelewski, Dominik
    Schober, Markus
    Faber, Kurt
    [J]. ORGANIC LETTERS, 2012, 14 (08) : 1974 - 1977
  • [57] Butein, a specific protein tyrosine kinase inhibitor
    Yang, EB
    Zhang, K
    Cheng, LY
    Mack, P
    [J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1998, 245 (02) : 435 - 438
  • [58] Purification and characterization of 2,6-dihydroxybenzoate decarboxylase reversibly catalyzing nonoxidative decarboxylation
    Yoshida, T
    Hayakawa, Y
    Matsui, T
    Nagasawa, T
    [J]. ARCHIVES OF MICROBIOLOGY, 2004, 181 (06) : 391 - 397
  • [59] Novel reversible indole-3-carboxylate decarboxylase catalyzing nonoxidative decarboxylation
    Yoshida, T
    Fujita, K
    Nagasawa, T
    [J]. BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2002, 66 (11) : 2388 - 2394
  • [60] Enzymatic functionalization of aromatic N-heterocycles:: Hydroxylation and carboxylation
    Yoshida, T
    Nagasawa, T
    [J]. JOURNAL OF BIOSCIENCE AND BIOENGINEERING, 2000, 89 (02) : 111 - 118